Potassium Iodide → [6-[5-(4-Trifluoromethyl-phenyl)-1H-pyrazol-3-ylmethoxy]-indol-1-yl]-acetic acid tert-butyl ester

HRID 915384

Reaktionsgleichung

Reaktionsgleichung von HRID 915384
[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:20][C:21]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[NH:23][N:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CN(C)C=O>[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:20][C:21]3[CH:25]=[C:24]([C:26]4[CH:27]=[CH:28][C:29]([C:32]([F:34])([F:33])[F:35])=[CH:30][CH:31]=4)[NH:23][N:22]=3)[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 69283069tert-Butyl (6-hydroxy-1H-indol-1-yl)acetateHCID 1785061113-Chloromethyl-5-(4-trifluoromethyl-phenyl)-1H-pyrazole

Produkt 1

HCID 178451203[6-[5-(4-Trifluoromethyl-phenyl)-1H-pyrazol-3-ylmethoxy]-indol-1-yl]-acetic acid tert-butyl esterAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of (6-hydroxy-indol-1-yl)-acetic acid tert-butyl ester (37 mg, 0.15 mmol), 3-chloromethyl-5-(4-trifluoromethyl-phenyl)-1H-pyrazole (43 mg, 0.16 mmol), cesium carbonate (54 mg, 0.16 mmol) and a trace of potassium iodide were suspended in N,N-dimethylformamide (4 ml). The suspension was stirred at ambient temperature for 14 h and for 4 h at 80° C. The solvent was evaporated under reduced pressure and the residue dissolved in 1 N HCl/ice water 1/1 and ethyl acetate. The layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined organic layers were washed two times with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, heptane/AcOEt) to give 5 mg (10 μmol, 7%) of the title compound as orange oil.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue dissolved in 1 N HCl/ice water 1/1
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted two times with ethyl acetate
  5. washThe combined organic layers were washed two times with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue purified by column chromatography (silica gel, heptane/AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-9ed5a382e2e74487b457e32e74dee025
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265149B2

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